Dan Springer, CEO of DocuSign

Dan  Springer founded Responsys in 2004 and after a
successful exit, he took  four years off to be a stay at
home dad. In 2017, Dan Springer joined  DocuSign as their
CEO. In this episode of Cloud Giants, Byron Deeter talks to Dan
about transitioning back to work, how to be a good leader,
setting boundaries, and how Dan increased DocuSign's value by $14
billion during his time as CEO.
Takeaways include:


As a leader, be aware of your gender bias:
“People make this construct around being a stay-at-home dad and
describe how strange it is,” Dan said. “Usually people say,
‘You were at the top of your game. All these people must be
calling you for these great deals.’ My feminist friends say if
I were a woman, people wouldn’t be asking that question. They’d
get, ‘Well, you should have been staying home with your kids
anyway.’ We should be aware we have these biases. I probably
had a little bit of that bias myself at the time, but I’ve been
educated. As we like to say, feedback is a gift. Thank you for
all the women and men who are great feminists that have given
me that perspective that I missed.”


Why ambiguity kills productivity for leadership
teams: “As a founder, be unbelievably clear on what
skills you’re bringing in and how the company is going to
change over time. Are you bringing in a COO who over time is
going to maybe grow into the CEO? Well, then how much time?
When will you know that person is ready? What will your new
role be? Get clarity on all those questions because most issues
arise when people are too polite and ambiguous.”


If you failed the first time, set the boundary the
second time: “As a person who is admittedly weak on
setting boundaries, this is a big lesson for me still,” said
Dan. “If someone shows up at my office or someone sends me an
email asking me for something, I say yes. I’ve learned to set
the boundary on the second time. I say, ‘Hey, happy to help. In
the future, I need you to do it this other way.’ For example,
we have all hands meetings every quarter where I speak to the
entire company and I also do town hall meetings in all our
offices. I try to drive people into those lanes where I’ve
already allocated the time. So that means if I’m visiting
customers, this isn’t the time for you to ask me about another
issue. I’m with a customer.”


Leadership is about understanding the trade
offs: “One of the biggest things that executive
leadership can provide is the ability to bifurcate the
discussion into which things are really competing with each
other and which things are independent,” said Dan. “If you get
down to each of those discussions, you’re able to find better
solutions because of the way you’ve framed the question.”